Finetuning pretrained large language models (LLMs) has become the standard paradigm for developing downstream applications. However, its security implications remain unclear, particularly regarding whether finetuned LLMs inherit jailbreak vulnerabilities from their pretrained sources. We investigate this question in a realistic pretrain-to-finetune threat model, where the attacker has white-box access to the pretrained LLM and only black-box access to its finetuned derivatives. Empirical analysis shows that adversarial prompts optimized on the pretrained model transfer most effectively to its finetuned variants, revealing inherited vulnerabilities from pretrained to finetuned LLMs. To further examine this inheritance, we conduct representation-level probing, which shows that transferable prompts are linearly separable within the pretrained hidden states, suggesting that universal transferability is encoded in pretrained representations. Building on this insight, we propose the Probe-Guided Projection (PGP) attack, which steers optimization toward transferability-relevant directions. Experiments across multiple LLM families and diverse finetuned tasks confirm PGP's strong transfer success, underscoring the security risks inherent in the pretrain-to-finetune paradigm.

Large language models (LLMs) remain vulnerable to multi-turn jailbreaking attacks that exploit conversational context to bypass safety constraints gradually. These attacks target different harm categories through distinct conversational approaches. Existing multi-turn methods often rely on heuristic or ad hoc exploration strategies, providing limited insight into underlying model weaknesses. The relationship between conversation patterns and model vulnerabilities across harm categories remains poorly understood. We propose Pattern Enhanced Chain of Attack (PE-CoA), a framework of five conversation patterns to construct multi-turn jailbreaks through natural dialogue. Evaluating PE-CoA on twelve LLMs spanning ten harm categories, we achieve state-of-the-art performance, uncovering pattern-specific vulnerabilities and LLM behavioral characteristics: models exhibit distinct weakness profiles, defense to one pattern does not generalize to others, and model families share similar failure modes. These findings highlight limitations of safety training and indicate the need for pattern-aware defenses. Code available on: https://github.com/Ragib-Amin-Nihal/PE-CoA